On your last point, I think you're perhaps being a little greedy (not in a terrible way).
Let's say your firm is worth $2mm now and you forsee it doubling and maintaining 100% growth rate next year, so it will be worth roughly $4mm. Even if it doubles several more times, you still don't have enough to launch a very ambitious future endeavor but all along you're risking a random decline in a huge, valuable, and concentrated asset.
Assuming your goals include having a family and secure financial life for yourself and them, I would be inclined to start taking money off the table as soon as I could be taking it off in $250m to $500m chunks. Not to say you need to sell it all, or even a controlling interest, but having had experiences of deep 6-figure losses in my trading account (which is extremely liquid 12 hours of every day with very low slippage), I know that I'd sleep a lot better with $300-500m off the table, and then get back to work growing the remaining 75% of the company into your multi-million.
I would seriously consider though still taking on your second big endeavor with outside investors. They have a way of keeping you honest and realistic, and if you can't convince outside investors, I wonder if it's prudent to wager your whole nut anyway.
Let's say your firm is worth $2mm now and you forsee it doubling and maintaining 100% growth rate next year, so it will be worth roughly $4mm. Even if it doubles several more times, you still don't have enough to launch a very ambitious future endeavor but all along you're risking a random decline in a huge, valuable, and concentrated asset.
Assuming your goals include having a family and secure financial life for yourself and them, I would be inclined to start taking money off the table as soon as I could be taking it off in $250m to $500m chunks. Not to say you need to sell it all, or even a controlling interest, but having had experiences of deep 6-figure losses in my trading account (which is extremely liquid 12 hours of every day with very low slippage), I know that I'd sleep a lot better with $300-500m off the table, and then get back to work growing the remaining 75% of the company into your multi-million.
I would seriously consider though still taking on your second big endeavor with outside investors. They have a way of keeping you honest and realistic, and if you can't convince outside investors, I wonder if it's prudent to wager your whole nut anyway.